Hydrochloric Acid → HCID 178524352, compound

HRID 434489Notes

Reaction equation

HRID 434489 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][PH:12]([CH2:14][O:15]CC)=[O:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([CH2:11][PH:12]([CH2:14][OH:15])=[O:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178473682HCID 178473682, compound

Product 1

HCID 178524352HCID 178524352, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.4 grams (0.34 moles) of the ethyl ester of 3-chloro-2-[(ethoxymethylphosphinyl)methyl]-benzoic acid prepared as described in Part B Step A of Example 1 was admixed with 20 ml of concentrated hydrochloric acid and 80 ml of dioxane. The resulting composition was saturated with hydrochloric acid (gas) and refluxed for 12 hours. The composition was concentrated, extracted with ether and the ether solution was dried over magnesium sulfate. The ether was evaporated and the residue was recrystallized from acetone/CH2Cl2 to give 7.5 grams (89% yield) of 3-chloro-2-[(hydroxymethylphosphinyl)methyl]-benzoic acid having a melting point of 219°-220° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. concentrationThe composition was concentrated
  3. extractionextracted with ether
  4. dry with materialthe ether solution was dried over magnesium sulfate
  5. customThe ether was evaporated
  6. customthe residue was recrystallized from acetone/CH2Cl2

Sources & evidence

ORD record
ord-fdd4f153ed554d9585b910121c88c149
Source dataset
uspto-grants-1983_08
Patent number
US04397790

Reaction notes

Loading…